Though he’s been a multiplatinum, Grammy-winning star for almost 20 years, Eminem is not an unequivocally triumphant figure, either within pop music or within his own mind. Just listen to the vulnerability and self-doubt on his recent single “Walk on Water.” At age 45, the Detroit rapper continues to make art about how people are driven crazy by weakness and lack. It’s just now he’s finding it harder to joke about the darkness that has always fueled his best work.

Some fans celebrate only the funny “Slim Shady,” when the musical comedy is quality controlled by executive producer Dr. Dre. They eschew the more viciously somber, rock-leaning character studies helmed by Em and his longtime Detroit collaborators Jeff and Mark Bass. But spend serious time with Eminem’s entire catalogue and you quickly realize that those two sides of his music are inextricable, one always informing the other.

When Eminem raps about violent, tragicomic death, he is furthering a grand murder-ballad tradition in folk and blues music. He’s also, on occasion, regurgitating grotesque sexist, homophobic stereotypes. But for a poor, white, emotionally unstable MC to excel in hip-hop and not be viewed as a villainous buffoon, he must possess prodigious artistic gifts and a real commitment to personal transparency. On these 50 essential songs, Eminem fearlessly displays that devotion to task and proves why he’s been one of pop music’s most fascinating, complex characters.

“Bully” (2003)

Appearing on the Internet sometime before its inclusion on the semi-official Eminem mixtape Straight From the Lab, “Bully” is the best of the loosies Eminem made during his virulent war of words with Benzino and Murder Inc.’s Ja Rule and Irv Gotti. He dismisses claims that he’s just a “2003 Vanilla Ice” by rhyming, “So now you try to pull the race card/And it backfires in your face hard/’Cause you know we don’t play that black and white shit.” Then he reflects on how death seems to hover over the genre, wondering if all the beef is worth it. He raps, “Now what bothers me the most about hip-hop is we so close to picking up where we left off with Big and Pac/We just lost Jam Master Jay, Big L got blasted away, plus we lost Bugz [of D12], Slang Ton [of the Outsidaz] and Freaky Tah [of Lost Boyz].”

“I’m Back” (2001)

“I’m Back” would appear high on a list of the most controversial Eminem songs: Even on the uncensored version of The Marshall Mathers LP, the rapper’s reference to the 1999 Columbine High School shooting – “I take seven [kids] from [Columbine], stand ’em all in line/Add an AK-47, a revolver, a 9/A MAC-11 and it oughta solve the problem of mine/And that’s a whole school of bullies shot up all at one time” – was bleeped out. Years later, Eminem got the last word, re-rapping the original line on “Rap God” from The Marshall Mathers LP 2.

But the track’s potency is barely impacted by the censorship, especially in the masterful first verse, which is giddy and assonance-heavy. “I used to give a fuck, now I could give a fuck less,” Eminem raps. “What do I think of success? It sucks, too much press/I’m stressed, too much sess, depressed/Too upset, it’s just too much mess, I guess.” Jay-Z later paid homage by borrowing this structure on his 2007 track “Success.”

“Bad Influence” (1999)

Eminem has always been adept at running dizzying circles around his critics, nullifying attacks by embracing and one-upping them. “People say that I’m a bad influence,” he raps on this track from the End of Days soundtrack. “I say the world’s already fucked, I’m just addin’ to it.” Though the beat by Jeff Bass is pedestrian and plodding, Eminem – the “human horror film, but with a lot funnier plot” – has no difficulty elevating it. He’s animated by his outsider status, aiming shots at the über-wealthy and hip-hop guide The Source: “As long as I’m on pills and I got plenty of pot/I’ll be in a canoe paddling, making fun of your yacht/But I would like an award/For the best rapper to get one mic in The Source.” He saves his best line for critics like Billboard editor-in-chief Timothy White, who condemned Eminem in 1999 for “exploiting the world’s misery.” “You probably think that I’m a negative person, don’t be so sure of it,” Eminem raps. “I don’t promote violence, I just encourage it.”

“Talkin 2 Myself” feat. Kobe (2012)

On this anguished highlight from Recovery, Eminem unburdens himself with honest, plainspoken revelations. “I almost made a song dissing Lil Wayne/It was like I was jealous of the attention he was getting,” Em admits. “Almost went at Kanye, too.” He doesn’t blame them for his loss of relevance at the dawn of the 2010s; instead, he criticizes his own uneven output, invokes the murder of his best friend Proof in 2006, and cites his addiction to prescription pills. “The last two albums didn’t count/Encore,I was on drugs, Relapse,I was flushing them out,” he confesses. Meanwhile, the rollicking, synthesized funk rock backing of Aftermath/Shady producer DJ Khalil plus Kobe Honeycutt’s tortured chorus heightens the interior drama. “[Eminem] told me that he literally had to pull everything out of himself to deliver that record because the music is so thick,” Khalil told Complex in 2011. “There’s so much music that he’s screaming at the top of his lungs.”

“Drug Ballad” (2000)

In the wake of The Slim Shady LP, Eminem became an A-list celebrity and the VIP debauchery quickly ensued: “The bigger the shows got, the bigger the after-parties; drugs were always around,” he recalled to Rolling Stone in 2011. But the theme that drives this song is that Eminem never moralizes or expresses regret but still recounts, in vivid detail, the dangers and illusions caused by drinking and drugs, including that his daughter might inherit his boozing ways: “That’s the sound of a bottle when it’s hollow, when you swallow it all, wallow and drown in your sorrow/And tomorrow you’re gonna wanna do it again.”

“Beautiful” (2009)

Eminem’s 2009 album Relapse, where he tried to recapture his salad days as the ribald storyteller Slim Shady, was generally considered a disappointment. But “Beautiful,” a self-produced track that he reportedly made while still addicted to prescription drugs, was poignant, confronting his frequent bouts with depression. Cuing up a heartening verse from Queen + Paul Rodgers’ “Reaching Out,” Eminem portrays himself as a modern Pagliacci who “hides behind the tears of a clown.” He balances his antipathy toward society with compassionate lyrical warmth. “In my shoes, just to see/What it’s like, to be me,” he sings in an achingly fragile voice. “But don’t let ’em say you ain’t beautiful/They can all get fucked, just stay true to you.” The rock-ballad melodrama of “Beautiful” points a way forward for what would be his true comeback, 2010’s Recovery. “I started writing the first verse and half of the second when I was in rehab going through detox,” he told The Guardianin 2009. “It brings me back to a time when I was really depressed and down, but at the same time it reminds me of what that space is like and what never to go back to.”

Busta Rhymes feat. Eminem, “Calm Down” (2014)

“It started off from just doing a dope, high energy hip-hop record into us respectfully competing and damn near battling each other,” Busta Rhymes told Complex about this flashy feat of technical abilities that took seven months. He says Eminem initially responded with a 42-bar verse, so he returned with 50 and the ante kept being raised – 60, 62, 64 – until it ended up as a tune where each rapper goes for about 2 minutes and 30 seconds apiece. “My hat is off to Eminem because he genuinely still cares about the music,” said Busta. “He very much cares about being a thoroughbred MC and wouldn’t ever be the type of artist that has to worry about letting me down or compromising his skill set because he’s trying to do something that people think is cool.”

Eminem, Slaughterhouse, Yelawolf, “Shady Cxvpher” (2014)

To promote the 2014 compilation Shady XV, the members of Slaughterhouse (Kxng Crooked, Joe Budden, Joell Ortiz, Royce Da 5’9″), Yelawolf and Eminem recorded extended a capella verses in their respective hometowns for Vevo in the 18-minute video “Shady Cxvpher.” In his seven delirious minutes, the rapper blends introspection (“Became a millionaire, went downhill from there”), breakneck double-time rhymes, tasteless barbs at media figures and some brutal honesty (“I think of all them times I compromised my bottom lines/And thought of rhymes that sodomized your daughter’s minds/Then I’m like: dollar signs.”)

“It’s about longevity. To me, the verse says, ‘After all the years of classic material, I am still one of the illest rappers to ever do this shit,'” Kxng Crooked tells Rolling Stone. “Being a wordsmith in rap music is a dying art. Connecting syllables, metaphors, punchlines and similes is a dying art. For those of us who still love rapping for the sake of showing how good one can rap, Eminem is our only mainstream voice.”

The Madd Rapper feat. Eminem, “Stir Crazy” (1999)

When Deric “D-Dot” Angelettie of the Hitmen – the production squad responsible for Bad Boy Records’ array of Nineties smashes – assembled his debut “Madd Rapper” album, Eminem was one of the few currently popular rappers with whom he hadn’t worked. “I called him up and said I was a fan of his, and he said he was a fan of mine, too,” D-Dot told MTV News in 1999. Collaborating with a then-unknown Kanye West as co-producer, the result is a loony game of wits between an upstart Slim Shady (fresh off his “My Name Is” success) and D-Dot’s churlish Madd Rapper persona. “Psyche, no bread/Fucked up in the head/Shot my girl and my sister ’cause I caught them in bed,” rhymes the Madd Rapper in a punchy Nuyorican flow reminiscent of the Beatnuts. But Eminem is clearly the superior stylist, dropping oddball stanzas like “I’m crazy with this razor/With this razor I’m crazy/With this crazor I’m razy/Razor cray, I’m crazy!” The Madd Rapper eventually concedes defeat: “Fuck that, Slim, keep that for yourself/You a crazy white dude and you need some help.”

The High & Mighty feat. Eminem, “The Last Hit” (1999)

As his fame ballooned at the turn of the millennium, Eminem was still reaching back to the (mostly East Coast) underground that had inspired and sustained him since before his 1996 debut album Infinite. Hence, this fiery boom-bap scratchfest from the Rawkus debut of Philadelphia duo High & Mighty. With samples of EPMD’s “Never Seen Before” and Hambone’s Salsoul disco-funk banger “Hey Music Man” lending the veneer of a vintage buddy-cop flick, Eminem trades bars with Mr. Eon. However, this is Slim Shady’s showcase and he goes bonkers, gobbling acid and snatching mics: “Escaped Bellevue, stuffed the nurse in a purse/Disperse like I added too many words in a verse.”

“My Fault” (1999)

The Slim Shady LP‘s 46-second “Lounge (Skit)” actually spurred Eminem to write “My Fault,” the intricate story song that follows it on the tracklist. The skit’s silly tune, sung by Bass Brothers producer Jeff Bass (“I never meant to give you mushrooms, girl”) got Em thinking about the time one of his friends had a bad drug trip. “He was talking about how worthless he was and how fucked up his life was,” Eminem said in the 2006 David Stubbs book Eminem: The Stories Behind Every Song. In “My Fault,” the friend’s gender is flipped into Susan, one of four characters Em alternately describes, comically and grotesquely, throughout the song’s narrative of a unruly rave party.

“Infinite” (1996)

The opening track of Eminem’s 1996 indie-label debut establishes his bona fides as a skillful, complex rhymer who specializes in visceral, imagistic lyrics. “I travel through your mind and to your spine like siren drills/I’m slimin’ grills of roaches, with spray that disinfects/And twistin’ necks of rappers/’Til their spinal column disconnects,” he snaps on the opening verse. Produced by D12’s Denaun “Kon Artis” Porter, Eminem’s voice has a more nasal timbre, balanced on a sumptuous sample of Les Baxter’s “Hot Wind” from the 1969 bikesploitation flick Hell‘s Belles. “If you ever listen to Michael Jackson before he was Michael Jackson, or Prince, they were younger-sounding, but you can tell there’s something there,” Jeff Bass, one-half of the album’s executive producers the Bass Brothers, told Rolling Stone. “When I hear Eminem from 20 years ago, I can hear Eminem today. I can hear the nuances in his tone, and his rhythm was insane, and this is him starting out as a kid. We recognized that there was something there that was special.”

“Stimulate” (2002)

An underrated gem, “Stimulate” appeared as a bonus track on the 8 Mile soundtrack, overshadowed by the more explicitly inspirational maxims of “Lose Yourself.” “Stimulate” methodically reflects the approach and attitude underpinning Eminem’s complex, singular human experience, conveying that sober message with the vitality of his comic rants. It’s a sound of regret and confidence, depletion and resolve, uncertainty and power, swirling in an unsteady cocktail. Rather than escalating any one mood, the song stays dysphoric and ambiguous. The woozy, flanging guitar tone and overall production suggests a sedated edginess, as Eminem’s voice shows signs of cracking. The sonic unease contradicts Em’s lyrics – “I’m just partying,” the Slick Rick-referencing “I’m just a man who’s on the mic” – as if he were recognizing that the expressive form he once loved had become its own kind of cage.

D12, “My Band” (2004)

On their highest charting single, Detroit horrorcore troupe D12, which Eminem joined in 1996 and used to develop his Slim Shady alias, addresses the rock-band malady of “lead singer syndrome.” “‘My Band'” is a parody, but as with any good joke, there are truths within it,” Touré wrote in a 2004 Rolling Stone profile of D12. “For example, at the concert, an unscientific poll of people in the VIP room found most couldn’t name any of the members of D12. A few recognized Bizarre, who stands out because of his twisted imagination, and Proof, well known to be Eminem’s best friend. But two people asked me if I was a member of D12.” The group was sanguine about the whole situation. “We grew up together, lived together, flipped burgers together,” Kuniva said of the relationship with Em. “We used to just sit on the porch and drink and think about hip-hop, think about makin’ it. There’s a bond there that nobody can break. … He knows [that] without D12 there wouldn’t be a Slim Shady.”

Missy Elliott feat. Eminem, “Busa Rhyme” (1999)

Missy Elliott was a key black artist to co-sign Eminem early on. “He hadn’t even come out with ‘My Name Is’ yet,” she said in a Billboard interview. “I heard something of his and instantly told [producer] Tim[baland], ‘I need this guy on my album … He’s special.'” Though the rappers were from different galaxies, Missy might be pop’s most hospitably freaky host; and here, she intros, sings the chorus, boosts the joie de vivre on the bridge and shouts support for her crude young guest. First up, Eminem blacks out in Slim Shady mode over Timbaland’s jovial synth-bass blurt. But after Missy interjects to lighten the mood, the shrewdly bold Timbaland switches mid-song into a dramatically charged, breakbeat chase scene: “I’m homicidal and suicidal with no friends,” Shady spits with sharpened mania. “Holding a gun with no handle, just a barrel at both ends … Fucking mad dog, foaming at the mouth/Fuck mouth, my whole house is foaming at the couch.”

OldWorlDisorder feat. Eminem, “3hree6ix5ive” (1998)

Before The Slim Shady LP, Eminem used the rap underground as a test audience for his new alter ego. One example features Skam, the Miami rapper-visual artist namechecked in “Stan,” under the group moniker OldWorlDisorder. Here, Slim Shady adopts an Andre 3000 lyric – “I’m just releasing anger!” – as his modus operandi. Another particularly gleeful example comes toward the song’s end: “I’ll take it back before we knew each other’s name/Run in the ultrasound and snatch you out your mother’s frame/I’ll take it further back than that, back to lovers’ lane/To the night you was thought up and cock-block your father’s game.” In a MySpace interview, producer DJ Spinna remembers Em being “on point and quiet.” Meanwhile, his barbs were becoming more distinctively violent and outrageous.

“Mockingbird” (2005)

Some critics dismissed this song from Em’s transitional fifth album Encore as just a mawkish exploitation of his daughter Hailie Jade. But what Eminem told Rolling Stone was “his most emotional song ever” was vulnerably fair-minded and delicately constructed. Here, he approaches the track like a stage actor digging into the nuances of a role, which is ultimately the key to our belief that he cares as much about being a real father as about being a privileged, embattled pop star firing cheap shots at his kid’s troubled mom. In other words, he keeps his bullshit in check and comes across like the everyday Marshall Mathers, a 32-year-old single dad still dealing with a dumpster-fire marriage, but also a mature adult who is capably raising three kids – Hailie, niece Alaina (who is also mentioned in the song) and half-brother Nate. What’s more, at least for this song, he makes that normcore guy just as compelling as the unhinged maniac he usually plays at work.

“Headlights” feat. Nate Ruess (2013)

Contrary to his well-earned reputation as a fearless cultural provocateur, Eminem has long written sentimental songs that give context and nuance to his emotional outbursts. “Headlights” from The Marshall Mathers LP2 may be the most necessary addition to this less-celebrated aspect of his canon because he finally tries to make amends with his mother – whom he had mocked mercilessly on 1999’s “My Name Is,” then excoriated, in heartbreaking fashion, on 2002’s “Cleanin’ Out My Closet.” Em’s use of Debbie Mathers as a musical antagonist frayed their relationship and resulted in a lawsuit, but on “Headlights” he apologizes for his part in their estrangement. “I went in head first/Never thinking about who what I said hurt/And what verse/My ma probably got it the worst,” he raps. He doesn’t downplay their brutal conflicts, like how she kicked him out on Christmas Eve when he was a teenager, and how they’ve barely spoken since his career took off. But he resists indulging in the kind of blind rage that he’s unleashed in the past. “I hope you get this message that I will always love you from afar,” he concludes. When asked about “Headlights” during a SiriusXM Town Hall session, Eminem responded, “What I said on the record is what I have to say about that. … There’s no need for me to elaborate on it.”

“Love Game” feat. Kendrick Lamar (2013)

This deranged dark comedy about how dangerous love can be isn’t what most fans expected from two of hip-hop’s most skilled lyricists. You can thank Rick Rubin, who sent Eminem the cheery, oldie-but-goodie loop (built on Wayne Fontana and the Mindbenders’ 1965 smash “A Groovy Kind of Love”) because he couldn’t hear anyone else over it. (“I don’t know if I want to hear Jay-Z on that record,” he said to Complex.) But it was Em’s idea to feature Kendrick Lamar, whom he’d recently met, to Rubin’s surprise. Even Em got more than he bargained for out of the collaboration. When the two MCs met at the studio, Eminem kicked out Lamar’s crew, as if to see whether his guest indeed wrote his own lyrics. Not only did Em get a hook and an outrageous Slim Shady-esque verse from Lamar, but he also had a song that forced listeners to reckon with the conceptual genius of both rappers.

“So Far” (2013)

In 2013, Jay-Z and Eminem became the first examples of what happens when the most famous rappers in the world are over 40. While the former embraced his maturity by collecting modern art and basketball arenas, Eminem brilliantly cut a figure as a confused hermit over the churning Joe Walsh riffs of “So Far.” Here, he raps about a fan noticing his crow’s feet, his inability to understand downloads and Facebook, and still feeling bad when pretty girls catch him picking his nose. Or, as he says to Zane Lowe, “I’m complaining about shit that I have no business really complaining about.”

“Love the Way You Lie” feat. Rihanna (2010)

The blockbuster collaboration between Eminem and Rihanna grew out of a loop that the British producer Alex Da Kid brought to songwriter Skylar Grey, which inspired her to write about her mistreatment by the music industry. When Eminem got the track, he wanted it for his Recovery album, but felt that only Rihanna could bring the necessary emotion. The song’s central metaphor shifted with Rihanna’s participation and became more explicitly about the violence that can erupt between two romantic partners – Eminem drew on his experiences with his ex-wife and lyrical foil Kim, while Rihanna’s memories of the violence at the hands of then-boyfriend Chris Brown tinged her unforgettable wails on the song’s chorus. “It’s something that we’ve both experienced on different sides of the table,” Rihanna told Access Hollywood in 2010. “[Eminem] pretty much just broke down the cycle of domestic violence, and it’s something that people don’t have a lot of insight on.”

Nicki Minaj feat. Eminem, “Roman’s Revenge” (2010)

On “Roman’s Revenge,” the throwdown between two of the 21st century’s most technically proficient crossover MCs, Eminem and the then-ascendant Nicki Minaj trade barbs (and au courant references to iPods and Giants quarterback Eli Manning, as well as a shout-out to Busta Rhymes’ verse on A Tribe Called Quest’s “Scenario”) over a malfunctioning-Nintendo beat crafted by Swizz Beatz. “Absolutely the most fun song on Pink Friday ­– it gave me life, dahling,” Minaj said, in her Roman Zolanski persona, during a 2010 MTV interview. After clarifying that she collaborated with “Slim Shady” not Eminem, Minaj was asked who offered up the “crazier” character. She broke up laughing and exclaimed, “It has got to be Slim!”

Bad Meets Evil, “Scary Movies” (1999)

For some, Royce the 5’9″ was still the best MC in Detroit in August of 1998, when he and Eminem paid a rite-of-passage studio visit to Stretch Armstrong and Bobbito Garcia’s influential New York underground radio show. Em and Royce flung freestyle spittle for 12 relentless minutes, stoked by what bystander Noah Callahan-Bever called “a pharmacopeia of drugs.” Just more than a year after that dazzling display and the transformative impact of The Slim Shady LP (which featured Royce on the track “Bad Meets Evil”), the duo released an indie 12-inch. The B-side, “Scary Movies,” was the keeper, a peak indie-’99 banger, with a strings-swept, RZA-gritty thump and some of Em’s most ferocious rhymes – “Any man plannin’ to battle’ll get snatched outta his clothes so fast it’ll look like an invisible man standin’.” But playing sidekick to Em didn’t suit Royce and their paths eventually diverged until an eventual rapprochement (and reunion album) after the 2006 death of their mutual friend, D12’s Proof.

“Without Me” (2002)

The de facto sequel to Eminem’s 1998 smash “My Name Is” and 2000’s “The Real Slim Shady” is a manic, quicksilver whirl through Eminem’s shit list, launching acid-laced broadsides and flipping the middle finger at real and imagined enemies, including then-Vice President Dick Cheney (whose wife Lynne took Em to task during a 2001 war of words with Madonna); DJ/producer Moby (who was “running his fucking mouth” at the Grammys, according to the rapper in a 2002 Rolling Stone interview); the Federal Communications Commission (which levied, and then rescinded, a fine against a Colorado radio station for playing the clean version of “The Real Slim Shady”); and his mom (who had taken him to court over his talk on “My Name Is”). “It’s, like, I need drama in my life to inspire me a lot, instead of just trying to reach for something,” Eminem told The Face in 2002.

“If I Had” (1999)

Eminem is known for his mania, his scorched-earth delivery, and for packing syllables into stuffed lines, but he is charmingly even-keeled on “If I Had.” That stems from the empty space in the production by the Bass Brothers, who helmed most of The Slim Shady LP. Their spare backdrops put a spotlight on Eminem’s tongue-twisting heroics. The rapper articulates a clear class consciousness, though of a type more often found in country music: “I’m tired of bein’ white trash, broke and always poor/Tired of takin’ pop bottles back to the party store/I’m tired of not havin’ a phone/Tired of not havin’ a home to have one in if I did have one on.” But don’t think he’s leading up to some final grandiloquent statement: “If I had one wish,” Eminem concludes, “I would ask for a big enough ass for the whole world to kiss.”

“Rap God” (2013)

Rap God” is a mind-boggling, seething testament to Eminem’s own legacy, the rapper executing one acrobatic lyrical trick after another to demonstrate, chronicle and critique his hip-hop lineage. However he seems to shrug whenever he talks about the song, which was recorded in one take. He says he barely remembers that session; for him, it was just another day of mapping out multiple internal-rhyme schemes. In the third verse of this six-minute exhibitionistic display, he famously references J.J. Fad’s “Supersonic,” rapping at a stunning, Twista-level of speed and agility. “Everybody, every time, when they make a song, wants to say: I’m still here. Don’t forget about me,” Em said to MTV News. Though his pop-culture references have occasionally dated him in the latter part of his career, “Rap God” acknowledges the past with a thrilling freshness.

“Brain Damage” (1999)

In “Brain Damage,” Eminem tells the tale of DeAngelo Bailey, a bully who terrorized him in junior high. And in April 1999, a few weeks after The Slim Shady LP hit the charts, the real DeAngelo Bailey stood up and granted an interview to Rolling Stone to confirm that the grisly, over-the-top song, where a young Marshall’s brain falls out of his skull, was at least somewhat based on factual events. “There was a bunch of us that used to mess with him. You know, bully-type things … We flipped him right on his head at recess,” Bailey recalled. But in 2001, after Eminem’s star had risen higher and his mother Debbie Mathers was awarded a small settlement over his lyrics, Bailey had a change of heart and sued the rapper, unsuccessfully, for $1 million.

“Wake Up Show Freestyle” (1997)

In 1997, a then-unknown Eminem flew to Los Angeles from Detroit to participate in the battle-rap competition Rap Olympics. With the event sparsely attended, DJs Sway and King Tech, hosts of the hugely influential WakeUp Show, agreed to put the rapper and other competitors on-air to help increase their exposure. Eminem’s two verses blended Big L-inspired multisyllabic mastery (“But I’m more toward droppin’ an acapella/To chop a fella into mozzarella worse than a helicopter propeller”) with blistering humor (The duo’s favorite line: “Doctor Kevorkian has arrived/To perform an autopsy on you while you scream, “I’m still alive!”)

“His verse stood out because it was hardcore, funny and skillful at the same time,” Sway and King Tech tell Rolling Stone via email. “Humor at that level was really new. People were more impressed with lyrical/metaphor masters at that time. He had that and was adding a weird humor to it, so he definitely stood out. The feedback for weeks was all positive. … We just remember driving home and saying, ‘That kid had mad skills, man. It was unusual but dope.”

“Criminal” (2000)

“‘Criminal’ was my new ‘Still Don’t Give a Fuck’ for The Marshall Mathers LP,” Eminem wrote in the 2000 book Angry Blonde. “That’s why it’s the last song on the record. It sums up the whole album.” Perhaps by design, “Criminal” comments on the controversy whipped up by Em’s debut, while at the same time ensuring that the follow-up album will generate even more outraged headlines. The first verse’s “Hate fags? The answer’s yes” was treated like a smoking gun in op-eds about Em’s homophobia, but that line, just like “Relax, guy, I like gay men” a few bars later, feels more like a shock-value punchline than a sincere declaration. Politically, “Criminal” is irresponsibly scattershot, but as a thesis statement for Eminem’s refusal of responsibility in the name of artistic license, it’s terribly on point.

“Any Man” (1999)

“So, I walk into D&D [Studios] and Eminem is sittin’ in the lounge – doesn’t look like a rapper, regular guy,” remembered producer Mr. Walt of Da Beatminerz (Black Moon, Black Star) in an interview with Hiphopdx. “I play beats for [Eminem] and he picks the beat for ‘Any Man.’ I never heard this guy rhyme [before]… So, he gets in the vocal booth and the first thing he says [in a high-pitched nasally tone] is ‘Hi!’ I look at my engineer like, ‘Oh my God, what did I just get myself into?'” Eminem goes on to unleash a series of wildly lewd and rude verses, as if he’s hoping to break as many taboos as possible in less than four minutes of classic New York boom bap. “I hope God forgives me for my sins,” he raps. “It probably all depends on if I keep on killin’ my girlfriends.” The session left Mr. Walt in a daze: “I looked at my engineer,” he said, “I was like, ‘Yo, what just happened?'”

“’97 Bonnie & Clyde” (1999)

If Eminem is the flawed hero of his own music, Kim, his ex-wife and mother of his daughter, Hailie, is habitually his Achilles’ heel. On “’97 Bonnie and Clyde,” one of the earliest and most explicitly chilling takedowns of his femme fatale, he plays loose with Bill Withers’ “Just the Two of Us,” fantasizing about dumping Kim’s dead body into the ocean … with his daughter in tow. Hailie even appears on the track. “I lied to Kim and told her I was taking Hailie to Chuck E. Cheese that day,” Em told Rolling Stone for a 1999 cover story. “But I took her to the studio. When she found out I used our daughter to write a song about killing her, she fucking blew.” Eminem knew the consequences that such a track could have for his daughter. “When she gets old enough, I’m going to explain it to her. I’ll let her know that mommy and daddy weren’t getting along at the time.” Years later, the rapper was more contemplative. “Shit, hindsight is 20/20,” he told RS in 2013. “At that time, that was how I dealt with things. I didn’t really think about … what was right or wrong or whatever.”

Jay-Z feat. Eminem, “Renegade” (2001)

Though it appeared on Jay-Z’s pinnacle achievement – 2001’s The Blueprint – the lyrically astounding “Renegade” was always Eminem’s song. He produced it and recorded the original version with Royce Da 5’9″ as the duo Bad Meets Evil. So, when Nas savaged Jay on 2001 diss epic “Ether,” charging that “Eminem murdered you on your own shit,” it was a distortion in more ways than one. In fact, Jay’s verse sketches lucid, entrancing metaphors that work both as introspection and inspiration. Plus, unlike every other major MC who appeared on a track with Eminem, he doesn’t strain to battle on Em’s gloriously spiteful turf. He follows his own artistic path. Good decision since Em’s tightly packed internal rhymes burst with assonance and he flows almost casually yet no less emphatically – that old familiar ire only pitching up his voice toward the end of his last verse so it feels more earned. On 2009’s “A Star Is Born,” Jay-Z gave his official blessing: “His flow on ‘Renegade,’ fucking awesome, applaud him.”

“Role Model” (1999)

More than any other major artist, Eminem has consistently toyed with and questioned the public’s desire to turn famous artists into paragons of virtue and wisdom. Here, he fires off absurd insults, injures himself and envisions scenarios where he’s embodying Norman Bates (“Mother, are you there? I love you”) or beating up Foghorn Leghorn “with an acorn,” hilariously satirizing the very idea that younger fans would ever mimic him. “To me it’s just a rap record. The message behind it was just complete sarcasm,” Eminem wrote in Angry Blonde. “I wanted to be clear: Don’t look at me like I’m a fucking role model.”

“White America” (2002)

By 2002’s The Eminem Show, the rapper had faced off against two consecutive vice-presidential wives (Tipper Gore and Lynne Cheney), in their crusades to censor rap. He strikes back in the album’s opening track, where he demands to know how he became one of America’s Most Wanted. In print, his interrogation of his position as a rich and famous white rapper seems almost matter-of-fact. (“It’s obvious to me that I sold double the records because I’m white,” he said to Rolling Stone.) But in “White America,” set to Em’s own arena rock-sized production – thudding percussion and the sound of fighter jets – those same sentiments feel like he’s declaring a state of emergency. “See, the problem is,” he raps urgently, casting himself as a generational figure, “I speak to suburban kids/Who otherwise woulda never knew these words exist/Whose moms probably woulda never gave two squirts of piss/’Til I created so much motherfuckin’ turbulence.”

“Marshall Mathers” (2000)

The song carrying Eminem’s birth name reveals the man behind all the personas as he struggles with paranoia and disgust for everyone who is now monitoring his every post-fame move. He petulantly jabs at bubblegum pop, boy bands and fellow Detroit pottymouths the Insane Clown Posse. “I felt that what I needed to talk about in the verses was just me and my opinions,” wrote Eminem in Angry Blonde. “So I touched on everything from the newest trends in hip hop (which I’m not really with), to ICP, to my mother, to my family members who don’t know me and always wanna come around. I wanted to just spit fire in each verse and have the soft-ass innocent chorus.” He did, in what came to be the mid-period Eminem style, entrancing millions with his passion and skill, while likely alienating others with his casual slurs.

“‘Till I Collapse” feat. Nate Dogg (2002)

Recorded circa “Lose Yourself,” this standout from The Eminem Show was built around the beat from Queen’s “We Will Rock You” and is, in many ways, a lyrical companion piece to 8 Mile‘stale of trial and toil. “You gotta search within you/And gotta find that inner strength/And just pull that shit out of you,” Em intones at the song’s outset. But it is Eminem’s ranking of the best all-time rappers, which comes halfway through the song, that made all the headlines. “I got a list … /It goes Reggie [a.k.a. Redman], Jay-Z, 2Pac and Biggie/Andre from Outkast, Jada, Kurupt, Nas and then me.” Chatter among pundits ensued, but Eminem was transparent about his respect for the genre’s greats. “Being a student of hip-hop, in general, you take technical aspects from [different] places,” he toldRolling Stone in 2013. “You may take a rhyme pattern or flow from Big Daddy Kane or Kool G Rap. But then you go to Tupac and he made songs. His fucking songs felt like something – “Holy shit! I want to fucking punch someone in the face when I put this CD in.” Biggie told stories. I wanted to do all that shit. My goal … is to be technically able to satisfy every underground or every great rapper there is and also be able to try to incorporate it into a song. And make the song feel like something.”

“Guilty Conscience” feat. Dr. Dre (1999)

“I remember Animal House when the girl passes out and the guy was about to rape her. He had a devil on one shoulder and the angel on the other saying don’t do it,” said Eminem, defending this song to the Los Angeles Times in 2010. “So, we did the same thing, only [with] a little more graphic detail.” On one of the most compelling tracks from The Slim Shady LP, Eminem introduces three different characters in three increasingly toxic scenarios with Emimen and Dr. Dre playing the characters’ good and bad consciences arguing with each other. The album version sounds like three creepy skits stitched together by voice-over, but the single version stacks three distinct eras of teenage desire: The chorus is inspired by the chaste yet spiritual “I Will Follow Him” by Sixties teenybopper Little Peggy March; Dre’s beat jauntily interpolates Ronald Stein’s “Pigs Go Home” from the Vietnam-era youth movie Getting Straight; while Dre and Em’s lyrical interplay speaks to the increasingly jaded and cynical MTV generation. References to Son Doobie of Funkdoobiest’s widely mocked foray into porn, the 1995 movie Kids and Dre’s own history of assault complete a deft satire of violent male impulses.

“Kim” (1999)

Though 8 Mile‘s “Lose Yourself” became Eminem’s Academy-Award-winning song, his most filmic performance was on this six-minute-plus dramatization of his own horrendously dysfunctional marriage to supposed true-love Kim Scott Mathers. His jealous, grindingly detailed rage surges and recedes in an abusive call and response, never losing intensity, as the Bass Brothers’ rock-centric track storms on. It climaxes at the end of the second verse, where he screams “Get the fuck away from me! Don’t touch me!/I hate you! I hate you! I swear to God, I hate you!” Then recoils, in tears: “Oh my God, I love you!” The “Kim” character (also played by Em) apologizes, but she’s blotted out by her husband’s howling cry. It’s as if John Cassavetes’ A Woman Under the Influence was reshot with Peter Falk’s husband in the spotlight instead of Gena Rowlands’ wife, replaying his climactic line, “I’ll kill ya, and I’ll kill these sons-o’-bitchin’ kids,” throughout a Tarantino-esque blood-spurting third act. Though overshadowed by its graphic depiction of violence against a woman, Eminem’s performance is powerful and intense. The real-life Kim reached a settlement after suing her husband for $10 million.

“Cleanin’ Out My Closet” (2002)

An innately combative MC, Eminem dreamed up his alter ego Slim Shady so he could unload on the world with impunity – morality police, music critics, other white rappers. But his true-north antagonists have always been wife Kim and mom Debbie. And of all the songs about his mother – both absurd and apologetic – “Cleanin’ Out My Closet” is the most deeply affecting, even becoming a Top Ten pop hit. DJ Head’s syncopated, almost delicate drum loop darts around the dark, spare instrumentation (bass, guitar, keyboards played by co-producer Jeff Bass), while Eminem excavates a lifetime of debilitating parental emotions. The song’s tone nimbly fluctuates, especially with the haunting “I’m sorry, mama,” chorus. Finally, there’s the climactic betrayal – when his mom, according to Em, tells him that she wishes he’d died instead of his uncle/best friend Ronnie (who committed suicide in 1991). Eminem barks his chilling reply into the void, “Well, guess what? I am dead – dead to you as can be!” In 2014, fellow Detroit native Angel Haze was inspired by to revive and revise “Cleaning Out My Closet” to tell her own tale, one of being sexually abused as a child. “I was so angry,” she told The Telegraph. “It was like catharsis to listen to [Eminem].”

“Get You Mad” (1999)

For this loony appearance on This or That, the Interscope-backed mixtape from influential Bay Area radio hosts Sway and King Tech, Eminem lays down a proper studio recording of some reference-packed bars initially spit for their Wake Up Show. Like the hip-hop version of his eventual pop-star takedowns, Em pokes fun at the latest round of rap dramas, takes down the current crop of platinum MCs, adds kindling to some of his earliest intra-industry feuds, throws out some tasteless jokes and lacerates the record business (“Don’t act like a fan, you wanna get signed/Get the whitest A&R you can find, pull him aside and rap as wack as you can”). “All we did was reach out to people that we knew were dope, and were gonna last,” producer King Tech told HipHopDX about making their 1999 compilation, which also featured early performances from Tech N9ne and Crooked I. “I’m from an era where if the beat is bangin’, just let him roll. Let him do what he does. I remember him callin’ me, ‘Tech, you think I gotta change the hook? I might’ve been too crazy.’ I was like, ‘Kid, I love that shit!'”

“Bitch Please II” feat. Dr. Dre, Snoop Dogg, Nate Dogg, Xzibit (2000)

Beyond some of the greatest collaborators of Dr. Dre’s solo peaks perfectly complementing each other, “Bitch Please II” captures the brash undercard confidence that makes Em’s unapologetic attitude so bracing. That take-me-or-leave-me armor works, in large part, because he constantly accents his cynicism with humor: his Snoop Dogg-tweaking opening lines and off-key Nate Dogg harmonizing envelope a stolidly serious Dre production in Em’s waggish glee. At his core, Eminem wants you to see that he’s just joking — “somewhere deep down there’s a decent human being in me” — without sacrificing any of his music’s outrageously rebellious spark and impact.